Sing Sing's original cellblock dates from 1825 and was constructed by the men who were eventually incarcerated inside of it. Though the museum preview center will open in 2022, the full museum, which will occupy the prison’s former power house and this original cellblock, won't open until 2025. 

Photo by Art Wolpinsky

Can This Prison Museum Tell the Full Story of Mass Incarceration?

Organizers imagine New York’s Sing Sing Prison Museum as a space that amplifies the voices of incarcerated people, family members, volunteers and prison staff.

Story by Emily Nonko

Published on

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Nascimento Blair lived inside Sing Sing Prison, in Ossining, New York, between 2011 and 2016. He began his pre-college education there, provided by the Ossining-based nonprofit Hudson Link, and went on to receive a bachelors in behavioral science and masters from the New York Theological Seminary. Soon after he left prison last April, he was invited to join a cohort of formerly incarcerated fellows at Columbia University’s Center for Justice.

As a fellow, Blair was asked to conduct research for the Sing Sing Prison Museum, a project under consideration for decades that has only recently gained traction. “I didn’t like it,” he said of the proposal. “I looked at it as another way to exploit prisoners, another way of Hollywood-izing prison where nothing is further from the truth. But I listened — because one thing I’m always good at is listening.”

Brent Glass, executive director of the museum, and Elias Alcantara, a museum board member, explained it was a priority to include voices of formerly and currently incarcerated residents of Sing Sing in the planning stages. They hoped fellows would conduct and record interviews with others impacted by the prison — formerly incarcerated people, their family members, volunteers and staff of the prison — so those stories could be integrated into the museum narrative. That narrative would attempt to weave Sing Sing’s history with larger topics around mass incarceration and the future of criminal justice.

The oral history project prompted questioning from the fellows and intense discussion: What was the purpose of the museum? Who was it for? How might it be influenced by the state, who owns the museum property and operates the adjacent prison? Why was a museum the right vehicle to tell the real stories, and real traumas, of mass incarceration?

Glass and Alcantara know these conversations are crucial, given the uniqueness of this museum in tackling the complex narratives and overwhelming impact of mass incarceration on the site of a working prison. “One of the questions we’re asking,” poses Glass, “Is why do we have prisons, what are prisons for?”

Eventually, the fellows decided to move ahead. For Blair, his decision came “because I have friends who are still there. I have friends who came home and have done brilliant, wonderful, progressive things. Those kinds of stories are never told.”

That kicked off an emotional process as Blair interviewed his mother, wife, the son of an incarcerated man, and the other fellows about how prison has shaped their lives. The conversations will all become part of Sing Sing Museum’s unique collection and historical narrative, as the board prepares to open the museum preview center in 2022 and the full museum, which will occupy the prison’s former power house and its original cellblock, in 2025.

Though a tremendous amount of work still needs to be done, with millions of dollars of funding still needed, this planning stage still offers opportunities for community building and healing around one of the country’s best-known, oldest prisons.

Brent Glass, executive director of the museum, leads a tour through the original Sing Sing cellblock. (Photo by Art Wolpinsky)

Perhaps the most intriguing component of this stage is that the museum lives as a vision, hope and promise for the people helping to build it. Because this country lacks intentional spaces to come together, contemplate and discuss the effects of mass incarceration, these visions often speak to something larger, regaining something that mass incarceration has taken away. Board member Lithgow Osborne, whose great grandfather was a reformist Sing Sign warden, envisions it as “a room with a big round table, and a lot of chairs, and people just pull up, we pick a topic, and we start talking.”

For Blair, it’s about continuing conversations like the ones he had with his family. “When you listen to these experiences,” he says, “You realize you’re not by yourself, even if you think you are, and [that] other people hurt with you.”

An Idea That’s a Long Time Coming, and Also Primed for This Moment

In 1813, Sing Sing became the first village in Westchester County chartered by New York State. In 1825, the state purchased a 130-acre site on the Hudson River and brought 100 incarcerated men to excavate marble from a nearby quarry and build the cellblock that would eventually house them.

The prison followed the “Auburn System” — in which the incarcerated were confined to solitary cells at night, worked during the day and were subject to physical punishment — as opposed to the “Pennsylvania System” of solitary confinement developed at the country’s other early prison, Philadelphia’s Eastern State Penitentiary.

Both Sing Sing and Eastern State established penitentiary models that influenced how modern prisons operate under mass incarceration. But both were left with crumbling infrastructure along the way. Eastern State, which closed in 1971, became a museum in 1995. At Sing Sing, the museum will occupy the now-empty 1936 powerhouse, which once provided the prison’s electricity, as well as the cellblock constructed by incarcerated workers in 1825. The 476-foot-long, roofless structure looks and feels like a bombed-out ruin; the crumbling marble and frayed barbed wire still holds the weight of punishment and isolation.

Sing Sing village changed its name to Ossining in 1901, trying to separate itself from the prison’s increasingly notorious reputation. Throughout the 20th century, the prison embedded itself into the American imagination, appearing in books, films and movies, and embodied the complicated juxtapositions of prison. While Sing Sing has long led the nation in reform through programming and education, for example, 614 people have been killed there on the electric chair.

At the start of the 21st century, Ossining officials began exploring ways to share the history through a museum. The plan faced roadblocks: as an active prison, there was concern the site would scare away potential visitors. Prison administration had its own hesitations. “There was pushback in talking about what was happening in criminal justice or what’s happening in prisons in general when you’re right next to an operating prison,” according to Ossining Town Supervisor and ex-officio museum board member Dana Levenberg. “It was a sensitive subject.”

The 2008 economic crisis slowed progress. When it picked up, there was interest among local politicians, prison administration and the inter-municipal organization Historic Hudson River Towns. “As criminal justice started rising in relevance, the project started picking up, getting more legs, and getting more people interested in looking at this [through] a different lens than just a museum or just the history,” explains Levenberg.

In 2015, the project secured $100,000 in state funds. Brent Glass, a national leader in preservation and museum interpretation, was hired not to simply oversee museum development, but to figure out the other roles that a site such as this needed to play. The board — civic, cultural and educational leaders in Ossining and the surrounding Hudson Valley, former members of prison administration, formerly incarcerated, victims and a family member of someone formerly incarcerated — all represent different viewpoints, but are in agreement this must be more than a traditional museum.

“I only represent one small sliver of history when it comes to Sing Sing, but my message has always been the history of Sing Sing needs to be told respectfully, and we should never, ever turn it into an easy thing for a baseball cap or keychain,” says Osborne, whose great-grandfather, Thomas Mott Osborne, became Sing Sing’s warden in 1914 with a reputation as a radical prison reformer.

“People are going to come see the prison because of its name, that’s terrific,” says former Sing Sing superintendent and board member Brian Fischer. “But once we get them there, our goal will be to ask the question: you’ve seen the history, what should we be doing tomorrow? We want to encourage people to ask: what’s next?” Fischer believes prisons represent something deeper about societal values: “Primarily, a prison is a reflection of society’s attitude toward criminal justice,” as he puts it. “Prison isn’t a static thing — they were created and changed over time as society changed.”

The interior of the now-empty, circa-1936 Power House. (Photo courtesy Sing Sing Prison Museum)

The changing landscape of prison museums shows visitors aren’t afraid of the question and reflection that follows. Eastern State Penitentiary, which focused on architecture and prison design in its early years, now includes a 16-foot-tall, steel graph representing the explosive growth of the country’s prison population between 1900 and 2020. The graph, installed in 2014, dramatically affected programming and prompted the museum to hire formerly incarcerated tour guides. Attendance doubled between 2014 and 2019, according to the museum’s senior vice president Sean Kelley.

“The graph changed the whole nature of the visit to the prison … at this point, we’re trying to work contemporary reflections into everything we do,” Kelley says. “We didn’t force this conversation — Americans are ready to have this conversation.”

Building Educational Bridges to the Surrounding Community

Sam North, a history teacher at Ossining High School, grew up in the shadow of Sing Sing without knowing anything about it. “Years later, that stuck with me,” he recalls. “There was absolutely [nothing] happening in the schools, or even in the community, connected with Sing Sing Correctional Facility.”

Ossining is now a modest suburban village located an hour north of New York City by train. The prison sits on the base of the waterfront with the village propped above; the two locations are further divided by MetroNorth railroad tracks. Unlike prisons in upstate New York, built in remote locations often surrounded by wilderness, it’s an easy 10-minute drive from pretty much anywhere in town down to the prison.

Despite that proximity, North notes, “It was just not a thing anybody talked about.” The museum is changing that. Glass began working with the school district while North was teaching a course on racism, classism and sexism. With guidance from Glass, he and other educators from Ossining and nearby Peekskill high schools developed two curriculums on mass incarceration, one that could be integrated into existing history courses and another to be taught as a standalone class.

In implementation, North says, “it felt like the district was dragging its feet, like it was still nervous to touch this particular topic.” In the meantime, he recruited students to help the Sing Sing Prison Museum team vet design teams for the future museum, given that the space will someday host school groups.

The district approved the class in the fall of 2020. North has since taught four sections of the standalone course for 84 students. He screens documentaries such as “The 13th” and “Just Mercy” and leads discussions around current-day topics that intersect with the criminal justice system. To engage his students around protests against police brutality, for example, North brought in local politicians to discuss and answer questions around police reform. In another class he showed “Zero Percent,” a documentary about the college program in Sing Sing, which was followed by a virtual visit with members of Hudson Link.

In the coursework, the students have been engaged with the museum’s progress: “They’re really savvy to [the location],” North notes, “They’re concerned about what the focus will be and how to make sure people won’t be glorifying prisons.”

North expects to teach the course fully in person this fall. Student feedback, so far, shows the class leaves an impact. “Throughout the semester my perspective has shifted completely on how people who make mistakes are punished, not only in the correctional system but in general,” one student wrote. “This is a topic that is not talked about enough, sadly, especially in a town that has a prison, and you did a very good job of delivering the information for the first time during times like these.”

Glass sees the relationship with the Ossining school district as indicative of more opportunities to strengthen the relationship of the village to the prison. “I’ve said to a number of public officials that Ossining can use this museum to, in effect, reinvent itself as a place where criminal justice reform is a forum,” he says. “Instead of being identified as a place of incarceration, as it has been for 200 years, use the museum and other places in Ossining to attract organizations devoted to criminal justice reform.”

Stephanie Lynn, a self-described “community builder” in Ossining and member of the board, spoke of a gardening program that takes place inside the prison. She envisions how a prison garden program could connect to greater Ossining with the help of the museum; perhaps introducing culinary programming inside prison while setting up employment at local restaurants for returning citizens. “We could have a museum restaurant, or a restaurant in town connected to the museum, that could be a launching point for jobs,” she suggests.

Two years ago Lynn worked with other community members and Sing Sing Prison Museum staff to present The Wait Room, a dance honoring the lives of women with incarcerated loved ones. Staged in the waterfront park that abuts the prison, the performance was a boots-on-the-ground effort, with a Hudson Link employee driving his van to the site every night to watch over the performance equipment. Still it attracted visitors from across the state, earning a review in the New York Times.

“The Wait Room,” performed in September 2019, explored the physical, psychic, and emotional toll that incarceration takes on women who have imprisoned loved ones. It was staged just outside the walls of Sing Sing Correctional Facility. (Photo by Fred Elmes)

The team faced challenges in aligning the event with the men incarcerated less than a mile from the performance. “The superintendent was originally going to let us advertise the event on the prison’s internal television system so men could tell their wives,” according to Lynn. “We intended to have a bus for the women visiting their husbands to bring them to performances.”

Because of an uptick in violence at the prison that summer, the prison’s superintendent quashed the plan. Instead, volunteers with the performance brought vans to the prison entrance and offered to drive departing visitors to the performance.

“Sometimes the fluidity between the prison and what we want to do can’t always happen,” explains Lynn, “Because of security restraints and concerns.”

Who Gets to Craft the Master Narrative?

That hurdle gets to a larger challenge the museum board faces: how to meaningfully connect the museum to the men incarcerated at the prison. It’s also unique, as there are few prison museums located on the site of a working prison. (The Museum of Colorado Prisons, located next to Colorado Territorial Correctional Facility, and the Angola Museum, at the Louisiana State Penitentiary, are two; neither present particularly nuanced looks at America’s relationship to mass incarceration.)

Board member Sean Pica, who was formerly incarcerated at Sing Sing and is now executive director of Hudson Link, has taken some of the responsibility. “When I speak to the guys on the inside about the project, I want them to know I’m on the board,” he says. “That they’re trying to include the voice of the men that live there makes it a very different kind of project from iterations in the past. I think the men are excited at the potential of capturing the history and voices of the other side.”

About a year ago, Hudson Link kicked off a word-of-mouth archive project “just spreading the word — we’d like your stories,” Pica says. “I don’t care if it’s about the mess hall, religion, family, write it down and get it to me.” These narratives, to be offered to Sing Sing Prison Museum, capture the kinds of prison stories rarely documented, Pica believes. And the board has been responsive to telling those stories. Pica characterizes his fellow board members as “a bunch of community members that happen to have a notorious max-security prison in their backyard, and want to capture [the experience] in a way that’s humanizing.”

Most of the focus, for now, has been centered on formerly incarcerated individuals. In his interviews as a Justice Center fellow, Nacimento Blair discussed with his mother what it was like for her in the prison visiting room, where she was disrespected by guards, and about providing for a son unable to work because of his incarceration. He hadn’t realized she kept many of her feelings and struggles from him as he worked to get through his prison term.

He spoke with a young man whose father is incarcerated about his feelings around having one parent missing, and if he was treated differently in school because of his father’s incarcerated status. Blair and his wife discussed the stigma of being married to someone incarcerated. Each of the other fellows he interviewed shared how they earned unofficial incomes inside, such as writing cards for prisoners who couldn’t read or write.

Blair hopes these conversations will help a future museum audience “understand the dynamics of punishment,” as he puts it. “We need to see how punishment doesn’t just impact the person doing the time, but it’s a whole community that’s affected.”

Interviews from the fellows — which also include interviews with a correctional officer and volunteers at the prison — will be used to craft the “master narrative” presented about Sing Sing and how it intersects with the larger history of mass incarceration. Glass believes this early work sets a framework for collaboration throughout the museum development, so that affected people have a final say on how the story is told.

In summer 2020 the museum launched Justice Talks, an online forum to discuss contemporary issues (wrongful conviction, solitary confinement, the impact of COVID-19) as well as historical topics such as the 1971 Attica Prison uprising. (Screenshot courtesy Sing Sing Prison Museum)

“Projects like our museum have to tell something that was supposed to be forgotten,” says Victoria Gonzalez, a museum staff member helping with research. She’s also dug into lesser-told histories of the more distant past, such as the women’s prison that operated in the mid-1800s.

So far, according to Glass, the New York Department of Corrections and Community Supervision has given the project free range, even though the museum board will need to work closely with administration to open the museum to the public. Sing Sing’s current superintendent, Mike Capra, is “100 percent behind the idea,” Glass says. “He’s even asked me if we could have a re-entry counseling office in the museum.” (The New York Department of Corrections and Community Supervision declined to offer an interview and issued a statement that “we support the vision of the project and believe the museum will provide visitors with a truly unique experience.”)

Before the Opening, Building Trust and Holding Space to Tell the Whole Story

For all the potential opportunities envisioned for the site, COVID-19 has taken an undeniable hit. Because of the pandemic and challenges in fundraising for the $45 million project, which requires a full rehabilitation and renovation of the power house and stabilization of the cellblock, the opening of the preview center was pushed back from the end of 2020 until the end of 2021. “I’d still call us a startup in many ways,” notes Glass. “Until we actually open that preview center, I won’t feel satisfied.”

But, as the pandemic tore through America’s prisons and the country erupted in protests following the murder of George Floyd, museum staff and board wanted to provide a forum for discussion. Last summer, the museum launched the first of its Justice Talks in collaboration with Ossining history teacher Sam North. For the first webinar, North brought some of his students from Ossining High School, as well as students from nearby Peekskill High School, to ask questions of local and state politicians. The conversation addressed issues of systemic inequality.

Over the past year, Justice Talks have covered contemporary issues, including wrongful conviction, solitary confinement and the impact of COVID-19, alongside historical topics such as the 1971 Attica Prison uprising.

Board member Ronnine Bartley organized a Justice Talk titled Families Staying Together. Barley married her husband Lawrence while he was incarcerated at Sing Sing, and they have a son. “The event is taking a look not how you go through the hardships or the barriers when you’re visiting, but how visiting consistently helps transform you or your family’s existence,” she says. “I’m sick of the negatives — if you keep putting the negative out there, that’s all people will believe.”

Still, Bartley has seen firsthand how prison operates to push people apart — families, friends, loved ones and entire communities. She knows of the division inside prison, too, such as between incarcerated residents and prison staff. She adds that even though correctional officers hold power over the people incarcerated, they’re negatively impacted by the system as well.

Glass characterizes this early work with the department as “building an environment of trust that we’re going to tell the story, the real story, good, bad and ugly, as long as we don’t ignore the effort they’re making now within the culture of reform.”

But there’s inherent tension even as Sing Sing and other prisons look to reform. Prison abolition has become a larger part of public dialogue since last summer’s uprising; the movement argues the country’s criminal justice institutions are incapable of reform. New York’s state prisons remain brutal and deadly — a reality made starkly clear during the pandemic. Can a prison museum, on prison property, tell that story about itself?

That final answer isn’t clear, but there are current topics agreed on by board members — from Sing Sing’s former superintendent to the man formerly incarcerated there. They point to the vast racial disparities in U.S. prisons, the ineffectiveness of an ever-growing prison population, the negative impacts of long-term sentencing and the effectiveness of supportive services over punishment. They emphasize the importance of developing an inclusive narrative of mass incarceration, as opposed to one crafted by the state. “The men that live at the prison will have a role, and a real voice, over what [future] exhibits look like and what the story being told feels like,” as Pica puts it.

In many ways, the museum’s planning process reflects America’s larger relationship to mass incarceration: widespread acknowledgment that it isn’t working, less clarity in how we fix it and how to address the overwhelming trauma it has caused. The museum, at the least, will be an intentional space to continue those discussions.

When Bartley ponders a future Sing Sing Prison Museum, she envisions togetherness. A learning space for children, alongside support and resources for prison staff and the formerly incarcerated. “You have a space here — everybody that’s involved in the criminal justice system has a space,” she emphasizes. “That’s how I visualize it, and I believe the rest of the board is visualizing that as well.”

Editor’s Note: This article has been updated to reflect Brent Glass’s current title as executive director of the museum.

This article is part of “For Whom, By Whom,” a series of articles about how creative placemaking can expand opportunities for low-income people living in disinvested communities. This series is generously underwritten by the Kresge Foundation.

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Emily Nonko is a social justice and solutions-oriented reporter based in Brooklyn, New York. She covers a range of topics for Next City, including arts and culture, housing, movement building and transit. 

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